Aisling House - Historic Hospitality
Entire home in Winchester, KY
Property details
Nestled within Winchester’s Thomson District, a nationally recognized historic place, Aisling House offers 7 bedrooms, an iconic porch, 1,700 square feet of patio, a greenhouse, chef’s kitchen and scullery, outdoor kitchen, and elegant gathering rooms across nearly 4,800 square feet. Convenient to Blue Grass Airport, Lexington, Keeneland, Kentucky Horse Park, Red River Gorge, and the Bourbon Trail.
INDOOR LIVING
- Multiple dining areas, formal dining room and ballroom
- Electric fireplaces
- 4-person sauna
- Historic library w/ original bookshelves
- 3 washer & dryer sets
- Desk workspace, printer, monitor
SLEEPING ARRANGEMENTS
- Bedroom 1: 1 king bed
- Bedroom 2: 1 king bed
- Bedroom 3: 1 king bed
- Bedroom 4: 1 queen bed
- Bedroom 5: 2 queen beds
- Bedroom 6: 1 king bed
- Bedroom 7 (Library): 1 king bed
OUTDOOR LIVING
- Front porch
- Outdoor kitchen w/ gas grill
- Outdoor dining, TV
KITCHEN
- Chef's kitchen w/ attached scullery
- 2 sinks, 2 dishwashers, 2 fridges (small & full-sized), industrial oven
- Drip/pod Keurig, moka pot
- Cooking basics, dishware & flatware
- Designed for kosher cooking
- Walk-in pantry
ACCESSIBILITY
- 3-story home, 10 steps to enter front door
- Step-free entry available via kitchen path from driveway
- 1st-floor bedroom & full bathroom
- While there are 10 steps at the front door, a step-free path leads from the driveway to the kitchen entrance and the first-floor bedroom
PARKING
- Long driveway (8 vehicles)
- Trailer, horse trailer & RV parking
Guests will have access to the entire property via keyless entry
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
SECURITY CAMERA INFORMATION
- 4 solar security cameras
- Location: front of the house, both driveways, gate to outdoor kitchen
- Coverage: whole property
Sleeping arrangements
Bedroom 1
1 king Bed
Bedroom 2
1 king Bed
Bedroom 3
1 king Bed
Bedroom 4
1 queen Bed
Bedroom 5
2 queen Beds
Bedroom 6
1 king Bed
Bedroom 7
1 king Bed
What’s included
Self check-in
Free parking on premises
Washer
Dryer
Central air conditioning
Central heating
Indoor fireplace
Kitchen
Guest reviews
Betty
September 2026
My name is Betty. I am an 82-year-old woman with disabilities. There are places I cannot stay because they are not handicap accessible. Recently, I stayed at Aisling House, which was a wonderful change. I stayed in a space that was accessible, with everything I needed on the first floor. The bathroom was beside my space and had all the things I needed at hand. Unless a person is handicapped, they do not realize how important these things are.
gwen
August 2026
We stayed the weekend of the Kentucky Derby and were transported back in time. The moment you entered the front doors you are taken back to the 1800's. With rich appointments and cozy beds. It was perfection. We stayed in the library and watched the race on the huge TV hung over the cozy fireplace. Our stay was more relaxing than can be imagined. The rest of the house was huge plenty of space for a family reunion. The chefs kitchen was a dream. Thankyou for sharing you home with us.
Sharon
July 2026
Unforgetable weekend in a beautifully restored Victorian home, perfectly appointed and decorated with period furnishings in every room except for 21st century beds, baths, and kitchen. Plenty of room for a small reunion or retreat. I will definitely reserve it again!
Cassie
July 2026
During my trip, I stayed in the dreamy attic room! The bathroom was an absolute sanctuary with a clawfoot tub with its fireplace view for a bath before curling up in the king-sized bed. A perfect experience after an evening spent on the terrace and out on the front porch for late-night rocking chair conversations. In the morning, the butler's pantry and kitchen are such a delight for their welcoming space and easy-going comforts. I loved this house. The library feels like a warm hug, and every room has something to offer here. I hope everyone picks out their favorite here.
Know before you go
House rules
Check-in: 4:00pm
Checkout: 10:00am
No pets allowed
Min. age to rent: 18Minimum age to rent: 18
No smoking
No parties